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Len Riley has over 20 years of experience in IT sourcing advisory and finance. Len worked at AMR Research as Vice President of IT Sourcing Advisory from January 1998 to July 2006. Len then joined CVS Health as Senior Director of IT Finance & Procurement in July 2006 and held this role until December 2014. In December 2014, they became the Chief Advisory Officer at UpperEdge, LLC, where they currently work.

Len Riley attended Bridgewater State University, where they obtained a Bachelor of Science degree in Business Administration with a concentration in Finance. The start and end years of their education are not specified.